NPASS Compound

Structure

CID212142 OpenBabel06191716002D 35 38 0 0 1 0 0 0 0 0999 V2000 -9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 6 34 1 0 0 0 0 7 10 1 0 0 0 0 7 18 2 0 0 0 0 8 9 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 27 1 0 0 0 0 12 30 1 0 0 0 0 13 19 2 0 0 0 0 13 21 1 0 0 0 0 14 20 2 0 0 0 0 14 23 1 0 0 0 0 15 20 1 0 0 0 0 15 24 2 0 0 0 0 16 19 1 0 0 0 0 16 25 2 0 0 0 0 17 21 1 0 0 0 0 17 26 1 0 0 0 0 21 28 2 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 28 1 0 0 0 0 25 34 1 0 0 0 0 26 29 1 0 0 0 0 26 30 1 1 0 0 0 27 29 1 0 0 0 0 27 33 1 1 0 0 0 28 35 1 0 0 0 0 30 5 1 1 0 0 0 30 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.27
Volume:	516.07
LogP:	6.357
LogD:	4.261
LogS:	-3.383
# Rotatable Bonds:	5
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.348
Synthetic Accessibility Score:	4.112
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.998
MDCK Permeability:	1.5342948245233856e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.731
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.65

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	99.49394989013672%
Volume Distribution (VD):	1.823
Pgp-substrate:	2.1499881744384766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.485
CYP1A2-substrate:	0.752
CYP2C19-inhibitor:	0.781
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.521
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.367
CYP2D6-substrate:	0.566
CYP3A4-inhibitor:	0.233
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	7.18
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.713
Human Hepatotoxicity (H-HT):	0.701
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.951
Skin Sensitization:	0.907
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.429
Respiratory Toxicity:	0.813

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC212142

Natural Product ID:	NPC212142
*Common Name:**	Schweinfurthin F
IUPAC Name:	5-[(E)-2-[(7R,8aR,10aR)-7-hydroxy-4-methoxy-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthen-2-yl]ethenyl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
Synonyms:	Schweinfurthin F
Standard InCHIKey:	BUFNPAYKUGAAAO-HLULBIOLSA-N
Standard InCHI:	InChI=1S/C30H38O5/c1-18(2)7-10-22-23(31)14-20(15-24(22)32)9-8-19-13-21-17-26-29(3,4)27(33)11-12-30(26,5)35-28(21)25(16-19)34-6/h7-9,13-16,26-27,31-33H,10-12,17H2,1-6H3/b9-8+/t26-,27-,30-/m1/s1
SMILES:	CC(=CCc1c(cc(/C=C/c2cc3C[C@@H]4C(C)(C)[C@@H](CC[C@@]4(C)Oc3c(c2)OC)O)cc1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376007
PubChem CID:	16721018
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(92)80315-6]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11421757]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15974621]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	Krachong waterfall area, Trang Province, Thailand	2001-APR	PMID[15974621]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[17326683]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17326683]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18844422]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18844422]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28972755]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	2
GI50	6
IC50	2

Activity Type	# Activity
Cell Line	7
CELL-LINE	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT571	Cell Line	A2780cisR	Homo sapiens	IC50	=	5000.0	nM	PMID[492996]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	=	10.0	nM	PMID[492997]
NPT380	Cell Line	U-251	Homo sapiens	GI50	=	13000.0	nM	PMID[492997]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	<	10.0	nM	PMID[492997]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	<	36.0	nM	PMID[492999]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	1500.0	nM	PMID[493000]
NPT1535	Cell Line	U-87 MG	Homo sapiens	EC50	=	240.0	nM	PMID[493000]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	410.0	nM	PMID[492997]
NPT26143	CELL-LINE	RPMI	n.a.	IC50	=	580.0	nM	PMID[492997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	1000.0	nM	PMID[492998]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC212142 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	482
0.1-0.2	1534
0.2-0.3	3630
0.3-0.4	8819
0.4-0.5	9882
0.5-0.6	4036
0.6-0.7	7967
0.7-0.8	5239
0.8-0.85	874
0.85-0.9	205
0.9-0.95	21
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC195561
0.9859	High Similarity	NPC158784
0.979	High Similarity	NPC2745
0.979	High Similarity	NPC302915
0.9722	High Similarity	NPC157783
0.9722	High Similarity	NPC325860
0.931	High Similarity	NPC473876
0.9241	High Similarity	NPC474397
0.9236	High Similarity	NPC472457
0.9236	High Similarity	NPC469557
0.9236	High Similarity	NPC90645
0.9189	High Similarity	NPC160196
0.9172	High Similarity	NPC233980
0.9167	High Similarity	NPC473845
0.9091	High Similarity	NPC35216
0.9085	High Similarity	NPC471388
0.9067	High Similarity	NPC80918
0.9067	High Similarity	NPC188578
0.9034	High Similarity	NPC50250
0.9034	High Similarity	NPC473108
0.9028	High Similarity	NPC59841
0.9028	High Similarity	NPC204347
0.9028	High Similarity	NPC323126
0.9028	High Similarity	NPC2613
0.9028	High Similarity	NPC475891
0.9021	High Similarity	NPC198038
0.898	High Similarity	NPC101376
0.898	High Similarity	NPC16269
0.898	High Similarity	NPC21776
0.8966	High Similarity	NPC474104
0.8958	High Similarity	NPC471389
0.8958	High Similarity	NPC265075
0.8951	High Similarity	NPC70682
0.8951	High Similarity	NPC260741
0.8944	High Similarity	NPC472800
0.8944	High Similarity	NPC173660
0.8926	High Similarity	NPC477612
0.8912	High Similarity	NPC471608
0.8912	High Similarity	NPC260397
0.8904	High Similarity	NPC45257
0.8904	High Similarity	NPC12641
0.8904	High Similarity	NPC469795
0.8904	High Similarity	NPC93323
0.8904	High Similarity	NPC280092
0.8904	High Similarity	NPC63879
0.8889	High Similarity	NPC234568
0.8889	High Similarity	NPC259519
0.8889	High Similarity	NPC27495
0.8881	High Similarity	NPC477938
0.8873	High Similarity	NPC61946
0.8873	High Similarity	NPC195022
0.8859	High Similarity	NPC211561
0.8844	High Similarity	NPC221318
0.8844	High Similarity	NPC181615
0.8836	High Similarity	NPC47633
0.8836	High Similarity	NPC477616
0.8836	High Similarity	NPC102044
0.8836	High Similarity	NPC85264
0.8828	High Similarity	NPC263261
0.8828	High Similarity	NPC87725
0.8828	High Similarity	NPC178054
0.8819	High Similarity	NPC127218
0.8819	High Similarity	NPC319647
0.8819	High Similarity	NPC25966
0.8819	High Similarity	NPC184613
0.8819	High Similarity	NPC245207
0.8819	High Similarity	NPC32630
0.8811	High Similarity	NPC162659
0.8811	High Similarity	NPC227503
0.8811	High Similarity	NPC248727
0.8811	High Similarity	NPC302701
0.8811	High Similarity	NPC16435
0.8811	High Similarity	NPC474639
0.8811	High Similarity	NPC265433
0.8811	High Similarity	NPC230734
0.8811	High Similarity	NPC306441
0.8811	High Similarity	NPC470802
0.8811	High Similarity	NPC270456
0.8811	High Similarity	NPC269091
0.8784	High Similarity	NPC475872
0.8784	High Similarity	NPC112251
0.8767	High Similarity	NPC107161
0.8759	High Similarity	NPC309124
0.8759	High Similarity	NPC184797
0.8759	High Similarity	NPC291101
0.8759	High Similarity	NPC266197
0.875	High Similarity	NPC176051
0.875	High Similarity	NPC211549
0.875	High Similarity	NPC266006
0.875	High Similarity	NPC474282
0.875	High Similarity	NPC107551
0.875	High Similarity	NPC326797
0.875	High Similarity	NPC276490
0.875	High Similarity	NPC102904
0.875	High Similarity	NPC103976
0.8741	High Similarity	NPC474206
0.8741	High Similarity	NPC112939
0.8741	High Similarity	NPC327382
0.8741	High Similarity	NPC151224
0.8741	High Similarity	NPC121812
0.8741	High Similarity	NPC234333
0.8741	High Similarity	NPC47398
0.8741	High Similarity	NPC473413
0.8741	High Similarity	NPC164787
0.8741	High Similarity	NPC470356
0.8741	High Similarity	NPC94750
0.8741	High Similarity	NPC260898
0.8741	High Similarity	NPC112246
0.8732	High Similarity	NPC263064
0.8725	High Similarity	NPC108811
0.8725	High Similarity	NPC202742
0.8725	High Similarity	NPC204770
0.8725	High Similarity	NPC262911
0.8725	High Similarity	NPC294558
0.8725	High Similarity	NPC236202
0.8725	High Similarity	NPC58190
0.8725	High Similarity	NPC70409
0.8725	High Similarity	NPC263940
0.8725	High Similarity	NPC170103
0.8725	High Similarity	NPC82917
0.8725	High Similarity	NPC18185
0.8707	High Similarity	NPC258083
0.8699	High Similarity	NPC247291
0.8699	High Similarity	NPC71046
0.869	High Similarity	NPC473739
0.869	High Similarity	NPC475836
0.869	High Similarity	NPC19869
0.869	High Similarity	NPC230124
0.869	High Similarity	NPC236306
0.869	High Similarity	NPC114171
0.869	High Similarity	NPC232164
0.869	High Similarity	NPC6300
0.8684	High Similarity	NPC21902
0.8681	High Similarity	NPC234952
0.8681	High Similarity	NPC126101
0.8681	High Similarity	NPC205442
0.8681	High Similarity	NPC472336
0.8681	High Similarity	NPC472334
0.8681	High Similarity	NPC476698
0.8681	High Similarity	NPC68292
0.8681	High Similarity	NPC327735
0.8675	High Similarity	NPC218041
0.8675	High Similarity	NPC182368
0.8675	High Similarity	NPC469706
0.8675	High Similarity	NPC145979
0.8675	High Similarity	NPC185955
0.8675	High Similarity	NPC9933
0.8675	High Similarity	NPC183380
0.8675	High Similarity	NPC225815
0.8675	High Similarity	NPC214326
0.8675	High Similarity	NPC469707
0.8675	High Similarity	NPC260781
0.8671	High Similarity	NPC478085
0.8671	High Similarity	NPC317380
0.8671	High Similarity	NPC473107
0.8667	High Similarity	NPC20757
0.8667	High Similarity	NPC227516
0.8658	High Similarity	NPC96576
0.8658	High Similarity	NPC324492
0.8658	High Similarity	NPC317053
0.8639	High Similarity	NPC175838
0.8639	High Similarity	NPC186033
0.863	High Similarity	NPC160283
0.863	High Similarity	NPC295719
0.863	High Similarity	NPC254759
0.863	High Similarity	NPC34431
0.863	High Similarity	NPC73505
0.863	High Similarity	NPC308768
0.863	High Similarity	NPC22317
0.863	High Similarity	NPC165026
0.863	High Similarity	NPC12668
0.8627	High Similarity	NPC78809
0.8621	High Similarity	NPC242715
0.8621	High Similarity	NPC56329
0.8611	High Similarity	NPC111655
0.8611	High Similarity	NPC472337
0.8611	High Similarity	NPC313081
0.8611	High Similarity	NPC256262
0.8609	High Similarity	NPC44452
0.8609	High Similarity	NPC476969
0.8601	High Similarity	NPC227719
0.8601	High Similarity	NPC85435
0.8601	High Similarity	NPC11060
0.8601	High Similarity	NPC475840
0.8601	High Similarity	NPC26394
0.8601	High Similarity	NPC92805
0.8601	High Similarity	NPC469610
0.8601	High Similarity	NPC211352
0.86	High Similarity	NPC320671
0.86	High Similarity	NPC328567
0.86	High Similarity	NPC320970
0.86	High Similarity	NPC327412
0.8592	High Similarity	NPC244888
0.8592	High Similarity	NPC472590
0.8592	High Similarity	NPC118683
0.8592	High Similarity	NPC164804
0.8592	High Similarity	NPC68205
0.8592	High Similarity	NPC293203
0.8592	High Similarity	NPC211413
0.8592	High Similarity	NPC103799

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC212142 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	860
0.2-0.3	1806
0.3-0.4	2698
0.4-0.5	1745
0.5-0.6	917
0.6-0.7	600
0.7-0.8	132
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8531	High Similarity	NPD1612	Clinical (unspecified phase)
0.8531	High Similarity	NPD1613	Approved
0.8521	High Similarity	NPD4907	Clinical (unspecified phase)
0.8521	High Similarity	NPD6410	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD4908	Phase 1
0.8322	Intermediate Similarity	NPD6674	Discontinued
0.8322	Intermediate Similarity	NPD4625	Phase 3
0.8322	Intermediate Similarity	NPD3027	Phase 3
0.8252	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD5844	Phase 1
0.8028	Intermediate Similarity	NPD4749	Approved
0.8014	Intermediate Similarity	NPD1610	Phase 2
0.7986	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD2861	Phase 2
0.7905	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD3620	Phase 2
0.7881	Intermediate Similarity	NPD6100	Approved
0.7881	Intermediate Similarity	NPD6099	Approved
0.7812	Intermediate Similarity	NPD37	Approved
0.7784	Intermediate Similarity	NPD7228	Approved
0.7778	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD4965	Approved
0.7778	Intermediate Similarity	NPD4966	Approved
0.7764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5735	Approved
0.7724	Intermediate Similarity	NPD6696	Suspended
0.7702	Intermediate Similarity	NPD1934	Approved
0.7683	Intermediate Similarity	NPD6234	Discontinued
0.7677	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD4060	Phase 1
0.7665	Intermediate Similarity	NPD6166	Phase 2
0.7665	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5494	Approved
0.7619	Intermediate Similarity	NPD7473	Discontinued
0.7616	Intermediate Similarity	NPD5124	Phase 1
0.7616	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1548	Phase 1
0.7603	Intermediate Similarity	NPD8651	Approved
0.7595	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD8127	Discontinued
0.7586	Intermediate Similarity	NPD4663	Approved
0.7562	Intermediate Similarity	NPD1653	Approved
0.7561	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6232	Discontinued
0.7543	Intermediate Similarity	NPD7906	Approved
0.7534	Intermediate Similarity	NPD5327	Phase 3
0.7518	Intermediate Similarity	NPD6671	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5283	Phase 1
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD6959	Discontinued
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7465	Intermediate Similarity	NPD7340	Approved
0.7457	Intermediate Similarity	NPD7549	Discontinued
0.7456	Intermediate Similarity	NPD2489	Approved
0.7456	Intermediate Similarity	NPD27	Approved
0.7451	Intermediate Similarity	NPD6353	Approved
0.7451	Intermediate Similarity	NPD4097	Suspended
0.745	Intermediate Similarity	NPD3018	Phase 2
0.744	Intermediate Similarity	NPD3051	Approved
0.7439	Intermediate Similarity	NPD2801	Approved
0.7434	Intermediate Similarity	NPD4140	Approved
0.7427	Intermediate Similarity	NPD7054	Approved
0.7415	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7311	Approved
0.7414	Intermediate Similarity	NPD7312	Approved
0.7414	Intermediate Similarity	NPD4578	Approved
0.7414	Intermediate Similarity	NPD4577	Approved
0.7414	Intermediate Similarity	NPD7313	Approved
0.7414	Intermediate Similarity	NPD7310	Approved
0.7403	Intermediate Similarity	NPD4538	Approved
0.7403	Intermediate Similarity	NPD4536	Approved
0.7403	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7240	Approved
0.7396	Intermediate Similarity	NPD2970	Approved
0.7396	Intermediate Similarity	NPD2969	Approved
0.7394	Intermediate Similarity	NPD7157	Approved
0.7384	Intermediate Similarity	NPD7472	Approved
0.7375	Intermediate Similarity	NPD7447	Phase 1
0.7372	Intermediate Similarity	NPD5763	Approved
0.7372	Intermediate Similarity	NPD5762	Approved
0.7371	Intermediate Similarity	NPD7309	Approved
0.7362	Intermediate Similarity	NPD4380	Phase 2
0.7351	Intermediate Similarity	NPD7095	Approved
0.7333	Intermediate Similarity	NPD5929	Approved
0.733	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3094	Phase 2
0.7312	Intermediate Similarity	NPD7212	Phase 2
0.7312	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7041	Phase 2
0.7312	Intermediate Similarity	NPD7213	Phase 3
0.7305	Intermediate Similarity	NPD7833	Phase 2
0.7305	Intermediate Similarity	NPD7831	Phase 2
0.7305	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2983	Phase 2
0.7297	Intermediate Similarity	NPD2982	Phase 2
0.7294	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7097	Phase 1
0.7278	Intermediate Similarity	NPD5177	Phase 3
0.7273	Intermediate Similarity	NPD3657	Discovery
0.7267	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7808	Phase 3
0.7254	Intermediate Similarity	NPD1398	Phase 1
0.7244	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5588	Approved
0.7244	Intermediate Similarity	NPD5960	Phase 3
0.7235	Intermediate Similarity	NPD3787	Discontinued
0.7233	Intermediate Similarity	NPD6331	Phase 2
0.7233	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4110	Phase 3
0.7233	Intermediate Similarity	NPD7466	Approved
0.723	Intermediate Similarity	NPD2981	Phase 2
0.7229	Intermediate Similarity	NPD7819	Suspended
0.7222	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2238	Phase 2
0.7202	Intermediate Similarity	NPD7075	Discontinued
0.72	Intermediate Similarity	NPD7251	Discontinued
0.72	Intermediate Similarity	NPD6559	Discontinued
0.719	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8053	Approved
0.7175	Intermediate Similarity	NPD8054	Approved
0.7168	Intermediate Similarity	NPD3818	Discontinued
0.7162	Intermediate Similarity	NPD1091	Approved
0.7162	Intermediate Similarity	NPD3092	Approved
0.716	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7152	Intermediate Similarity	NPD4624	Approved
0.7143	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD7768	Phase 2
0.7143	Intermediate Similarity	NPD5058	Phase 3
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD7124	Phase 2
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7135	Intermediate Similarity	NPD6071	Discontinued
0.7126	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8455	Phase 2
0.7126	Intermediate Similarity	NPD1465	Phase 2
0.7126	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3892	Phase 2
0.7125	Intermediate Similarity	NPD4628	Phase 3
0.7123	Intermediate Similarity	NPD7741	Discontinued
0.7123	Intermediate Similarity	NPD3091	Approved
0.7117	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD228	Approved
0.7108	Intermediate Similarity	NPD6072	Discontinued
0.7107	Intermediate Similarity	NPD2424	Discontinued
0.7101	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1511	Approved
0.7092	Intermediate Similarity	NPD4750	Phase 3
0.7091	Intermediate Similarity	NPD4005	Discontinued
0.7083	Intermediate Similarity	NPD2563	Approved
0.7083	Intermediate Similarity	NPD3817	Phase 2
0.7083	Intermediate Similarity	NPD2560	Approved
0.7083	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7294	Phase 1
0.7078	Intermediate Similarity	NPD7985	Registered
0.7075	Intermediate Similarity	NPD1357	Approved
0.7069	Intermediate Similarity	NPD3751	Discontinued
0.7066	Intermediate Similarity	NPD5722	Discontinued
0.7063	Intermediate Similarity	NPD7635	Approved
0.7063	Intermediate Similarity	NPD7843	Approved
0.7063	Intermediate Similarity	NPD1652	Phase 2
0.7059	Intermediate Similarity	NPD5709	Phase 3
0.7055	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6355	Discontinued
0.7048	Intermediate Similarity	NPD4678	Approved
0.7048	Intermediate Similarity	NPD4675	Approved
0.7047	Intermediate Similarity	NPD3705	Approved
0.7047	Intermediate Similarity	NPD1611	Approved
0.7044	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6584	Phase 3
0.7033	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8156	Discontinued
0.7027	Intermediate Similarity	NPD4626	Approved
0.7022	Intermediate Similarity	NPD8313	Approved
0.7022	Intermediate Similarity	NPD8312	Approved
0.7021	Intermediate Similarity	NPD2684	Approved
0.7019	Intermediate Similarity	NPD3750	Approved
0.7019	Intermediate Similarity	NPD8166	Discontinued
0.7018	Intermediate Similarity	NPD4666	Phase 3
0.7017	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7526	Approved
0.7012	Intermediate Similarity	NPD6090	Discontinued
0.7012	Intermediate Similarity	NPD52	Approved
0.7012	Intermediate Similarity	NPD1512	Approved
0.7012	Intermediate Similarity	NPD6273	Approved
0.7012	Intermediate Similarity	NPD7314	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data